Apologies, our sales department is a little backed up at the moment. Looks like someone responded to your initial concerns though.
Classic is all our applications, hosted on your own machine. Classic does not include Courses, our "live" feature items, video encoding, and some other features which are cloud only at this time.
You would need to have an active license but you will gain access to version 5, at this time.
It is Cloud only at this time. There are no plans to change this.
To gain access to software upgrades, support, the spam defense system, GEO IP address, etc... requires an active license.
Yes, that is a Core feature.